If you lived through the era of Rachel haircuts and grunge, you no doubt remember couples like Brad and Jennifer, Johnny and Winona, and Britney and Justin, who dominated the headlines for a time and won our hearts. But do you remember Luke Wilson and Drew Barrymore? (No?) Or what about Ashton Kutcher and January Jones? And who can forget the short-lived fling between Matthew Perry and Julia Roberts? Well, it turns out, we can.
For a list of star-studded pairings so random they’ll definitely make you jog your memory, slip on your best flannel, and read on—and get ready for a romantic stroll down memory lane. And for more Hollywood romance, check out these 15 On-Screen Couples Who Hate Each Other in Real Life.
After starring together in 1996’s A Time to Kill, these actors sparked a romance, though Sandra Bullock constantly insisted that the pair were only friends (though the tabloids apparently saw something a little more cozy than chumminess).
Singer Seal seems to have an affinity for gorgeous supermodels. Before eventually marrying Heidi Klum, he was briefly spotted with Tyra Banks at several big Hollywood events in 1996—though the romance ultimately fizzled out. And for more sizzling chemistry on and off the silver screen, check out these 20 Onscreen Couples Who Dated Off-Screen.
Before officially coming out in 2006, actor Neil Patrick Harris dated Christine Taylor, admitting afterward to Howard Stern that she was the “coolest, nicest chick ever” and his less-than-romantic feelings for her confirmed his suspicions that he was, in fact, gay.
After guest starring in a 1996 episode of Friends where she played Chandler Bing’s love interest, Julia Roberts seemed to have grown fond of the actor behind the character. The pair were spotted on several dates later that year, though nothing of substance came from their romantic interactions. And for more strange love affairs, check out these 20 Celebrity Couples With Huge Age Gaps.
Just as Ryan Reynolds was beginning to emerge in the Hollywood scene, he met 3rd Rock From the Sun funnywoman Kristen Johnson and they began a romantic relationship that lasted a few months between 1999 and 2000. And for more bits of 90s nostalgia, check out these 30 Funniest Jokes About Growing Up in the ‘90s.
Richard Gere and Cindy Crawford quickly became one of the most famous (and attractive) couples to ever walk the red carpet in the ’90s. They began dating in 1987 when Crawford was only 21 and Gere was 38—a 17-year difference in age that would eventually contribute to the failure of their four-year marriage in 1995. Decades later, Crawford spoke about the nature of the relationship on Marc Maron’s WTF podcast, admitting that she had been too young then to truly fall in love. “And then, as I started kind of growing up and growing into myself—it’s hard to change the nature of a relationship once you’re already in it,” she said.
You might forget about this marriage between Gary Oldman and Uma Thurman—mostly because they went on to pursue more dramatic love interests (for Thurman, Ethan Hawk, and for Oldman, well, two more marriages). They were married from 1990 to 1992.
Though N’SYNC boy band member Lance Bass came out as gay in 2006, he was still in the habit of keeping up appearances when he dated actress Danielle Fishell back in 1999. The pair even went to prom together before calling it quits just a year later in 2000.
Chris O’Donnell and Reese Witherspoon were still fresh-faced youngsters when they began dating in 1992. Though they dated for only a few months, the media loved to capture images of their innocent affection for one another. After Witherspoon, O’Donnell moved on to the next woman, Caroline Fentress, who turned out to be the love of his love—they’re still married years later.
Shortly after declaring “Yep, I’m Gay” on the cover of Time Magazine in 1997, Ellen DeGeneres began dating fellow actress Anne Heche. Until their split just three and a half years later, the two women were constantly declaring their love for each other openly, with DeGeneres even saying, “If Anne goes, I want to go. That’s how strongly I feel.”
It’s obvious that costars Matt Damon and Minnie Driver’s on-screen chemistry on Good Will Hunting eventually transferred over into their personal lives, as the two were a pair for seven months after filming wrapped in 1997. Though, the romance was short-lived because Damon reportedly hooked up with Winona Ryder at a New Year’s Eve Party—and entered into a three-year relationship with the actress without telling Driver that they were through.
This unlikely pair began dating in 1996 when Liv Tyler was filming scenes for Woody Allen’s Everyone Says I Love You with Leonardo DiCaprio’s best friend, Lukas Haas. And, though her scenes were eventually removed from the movie, her brief but intense relationship with DiCaprio made it all worth it—or at least we’re assuming so.
Before Sheryl Crow’s seemingly tumultuous relationship with Lance Armstrong, she kept her cool with actor Owen Wilson back in the 90s. For a point in their relationship, the duo even made music together, until Wilson broke things off, leading the singer on to create more inspiring breakup ballads (so we might be more thankful for the breakup than Crow, admittedly).
These two R&B legends tied the knot just a few weeks after meeting at a Bad Boy Records photo shoot. Like many others on the list, this relationship proved to be equally rewarding and volatile for the pair, with Notorious B.I.G. eventually dragging Faith Evans into the East Coast/West Coast rap beef that some say ultimately led to his murder in 1997, just a few months after the couple divorced.
Before Mad Men star January Jones even made her acting debut in 1999, she was romantically linked to Ashton Kutcher, who was also just beginning his foray into the world of the dramatic arts. As it turns out, the relationship wasn’t exactly benefitting both actors, as Jones told GQ in 2009, “The guy I was dating when I first got to L.A. was not supportive of my acting. He was like, ‘I don’t think you’re going to be good at this,'” she said.
Similar to the playboy he acts out on many of his various roles, David Spade is legendary for all of his Hollywood conquests—though this is the one that ultimately began it all. The pair were spotted together between 1996 and 1997.
When speaking about her three-year relationship with Joaquin Phoenix, Tyler has often called him her “first love” and Phoenix has said very similarly sweet things about his Inventing the Abbotts costar.
Apparently, Drew Barrymore fell victim to Luke Wilson’s handsome drawl and sweet down-to-earth nature. The couple met in 1997 while filming Home Fries and dated for two years before splitting up in 1999.
In the end, this relationship (or, at first, affair) between Ted Danson and Whoopi Goldberg ended up costing the married Danson $30 million for his indiscretion. Though the pair met in 1988 when they were both guests on Arsenio Hall Show, it wasn’t until they starred together in Made in America that a romance developed between the two—though Danson was married to Cassandra Coates at the time. Despite a fiery start to the relationship, it ultimately ended in 1993.
Though the pair doesn’t exactly get along famously today, they were once an item in the 1990s, before either of their careers had garnered any acclaim.
Michael Keaton and Courteney Cox met in 1989 and quickly became one of the most high-profile couples of the 90s. Despite their efforts to keep their relationship private, the couple was constantly plagued by the paparazzi, attempting to snap an intimate photo of the pair. After six years of dating, the couple split in 1995—and they appear to still be on good terms with one another. Shortly after the breakup, Cox spoke of her fondness for Keaton. “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” she told People.
Before Drew Barrymore romanced nearly half of Hollywood, she dated her Everyone Says I Love You co-star, Edward Norton. The pair dated on and off between 1996 and 1999 before eventually calling it quits.
This indie power couple began dating the same year that they formed the cult rock ‘n roll band Sonic Youth in 1981. Quite quickly, Thurston Moore and Kim Gordon became the parents of the indie underground, lending their guiding hands to the creation of other groups citing their band as an influence. Though, unfortunately, it seems all good things come to an end. In 2001, the pair announced the end of their relationship—and the end of Sonic Youth.
This power couple met in 1992, and for more than a decade until their split, likely bonded over their affinity for directing beautiful and complicated indie films with impeccable soundtracks. After their divorce in 2003, the pair were rumored to have created characters in their films that resembled each other in tribute.
The relationship between Carson Daly and Jennifer Love Hewitt can be characterized as mostly uncomfortable, culminating in a series of awkward encounters after their breakup in 1999. Though Daly thought that things were going swimmingly with his girlfriend, she didn’t seem to feel the same way when she announced that the pair were breaking up while speaking on Howard Stern’s radio show.
When two of the most prolific ’90s musicians united, the world only seemed to yawn. Sure, Madonna was great—but Vanilla Ice? We’re pretty sure that she could have done much, much better.
Often called one of the coolest and “dorkiest” couples of the ’90s, Paul Thomas Anderson and Fiona Apple mixed work with pleasure, spending much of their three-year relationship collaborating, with Anderson directing many of Apple’s music videos. And, though their relationship ended in 2000, the pair reunited a decade later to direct the musician’s video for “Hot Knife.”
The pair met in 1991, married in 1992, and were divorced just two years later. According to Abdul, the relationship ended because Estevez, already a father of two from a previous marriage did not want any more children—though she did.
Model Claudia Schiffer felt a magical attraction to David Copperfield—quite literally, at first. They first met in 1993 when he brought her up on stage to participate in a mind-reading act and flying illusion—and they were engaged just a year later. As it turns out, the spell only lasted until 1999, when the pair eventually called it quits.
For actor Matt Dillon, there’s just something about Cameron Diaz. They started dating in 1995 and starred together in There’s Something About Mary three years later—then broke things off after filming wrapped. And for more from last century’s most wacky decade, learn 20 Slang Terms From the 1990s No One Uses Anymore.
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